(E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate → Ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)propanoate

HRID 1909549Notes

Reaction equation

HRID 1909549 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 58566652(E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58566596Ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution (E)-ethyl 3-(5-hydroxy-[1,1′-biphenyl]-2-yl)acrylate (652) (420 mg, 1.57 mmol) in ethanol (6 mL) was added Pd/C (42 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred overnight at room temperature, was filtered through a pad of celite and concentrated in vacuo to give ethyl 3-(5-hydroxy-[1,1′-biphenyl]-2-yl)propanoate (653).

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationwas filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5361511844de4c84b7d7097867e3d533
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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